For Comedy Week, we're running a handful of tributes in the vein of our Dead Wrestler of the Week series. Here, the Masked Man looks at the legacy of Mitch Hedberg, the surrealist who developed a cult following before his death in 2005—and an even bigger one after his death.

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Calling someone a comic's comic is just damning them with great praise. People always bestow titles like that on respected but under-successful figures in their fields—writer's writer, actor's actor—and for all the good intentions of the sentiment, it's just a shrug, a way of saying that the people who matter love you, even if nobody else does. It's saying that a guy will never make it because he'll never sell out, regardless of whether or how often he's tried to do just that. It's saying your talent outpaces the public's ability to appreciate it. The note of self-congratulation is unmistakable. A comic's comic is good at telling jokes that the guys in the industry like. That's a skill, but it's not precisely a profession.

For much of his career, Mitch Hedberg was a Comic's Comic. Then he died.

To be fair, he was pretty popular by the time he died, in March 2005, of "multiple drug toxicity." He was 37. He was touring basically nonstop and nearly selling out everywhere he went. But he hadn't found a place in the mainstream. At least nothing like the place he's found since his death.

Back then, if he wasn't a Comic's Comic, he was a Stoner Comic or a Slacker Comic—both of which refer mainly to his look and style and are about as helpful in describing him as calling him a White Comic or a Sunglasses-Wearing Comic—or, worst of all, an Average Guy Comic, which always evokes for me the milquetoast stylings of Dane Cook or Stephen Lynch, guys in untucked button-downs with the lousy hair of a skirt-chasing college guy and the wry sensibility of his fat friend. But if Average Guy isn't quite right, it's somehow more accurate than the others.

By all accounts, Mitch Hedberg was a pretty regular guy. He grew up in St. Paul, Minn., before he ditched the suburbs for a peripatetic life, literally leaving his parents' home without telling them after high school graduation because he didn't know how to tell them he was going. He surfaced in Fort Lauderdale, Fla., eventually taking up kitchen work and trying his hand (very) unsuccessfully at open mic comedy nights in the area. (His first show was in Boca Raton.) He soon got his footing, whereupon he picked up again and moved to Seattle. It was there that he started to get some recognition. He begged his way onto MTV's short-lived Comikaze, and even though the show didn't last, Hedberg was on his way: In 1996, he got the big-time break of appearing on Letterman; in 1997, he won the grand prize at the Seattle Comedy Competition; in 1998, he stole the show at the "Just For Laughs" festival in Montreal.

On paper, Hedberg's jokes come off like a heady and slightly trippy Twitter feed—you laugh, but you don't necessarily remember. It was in his execution that the jokes took flight. (And while I acknowledge that describing Hedberg's style in print is bound to be as unsuccessful as reading his jokes, allow me to hazard an attempt.) Hedberg had developed a style of awkward, scattershot, observational koans that weren't exactly one-liners; he was a minimalist, sure, but he was working on another level than, say, Henny Youngman. His jokes weren't just riffs on existing tropes. The only norm Hedberg adhered to was that there weren't any norms. His humor never met you halfway. He pulled listeners into his own head. His deliver was as off-putting as was his material, but you still came away marveling at the intelligence and precision of observation—to borrow from Edward Ruscha, his was the sort of art that elicits a "Huh? Wow!" as opposed to a "Wow! Huh?" That was his brilliance.

The obvious point of comparison is with Steven Wright, and—again, on paper—the two comics seem to share a lot in common. But where Wright was a comic golem, an android programmed to tell off-putting jokes, Hedberg was, in an odd way, emotionally accessible. As off-beat as most of his jokes were, they were presented in the manner of an oddball childhood friend you haven't seen in years, or, as Paul Brownfield put it in the Los Angeles Times, like "a socially awkward person trying to start dinner conversation." Though dressed in the garb (both literally and metaphorically) of the turn-of-the-century hipster, Hedberg's jokes were decisively un-ironic; he wasn't engaging in social commentary or wry negativity so much as he was baring his weirdo soul. The "stoner" label is inaccurate, but even the occasional drug user could identify: Hedberg was you, high, thinking you're funny—and actually being funny.

And that's how he won us over. The way he stood on stage, eyes closed, sunglasses on, bangs over his face, halfway trembling—he was just as shy as we would've been in his position. (As he told Joel Stein in 1998: "I don't like to connect with the crowd. I find that if you look at people's faces, you see a disappointed face.") He was an underachiever—he looked that way, sure, but his minimalist style, as good as it was, always seemed to imply a disinclination to longer-form work. ("Sometimes in the middle of the night, I think of something that's funny, then I go get a pen and I write it down. Or if the pen's too far away, I have to convince myself that what I thought of ain't funny.") He broke the fourth wall—repeatedly—in an attempt to reposition himself from alone on stage to seated among his own audience: "That's like a carbon copy of the previous joke but with different ingredients. I don't know what I was trying to pull off there." "That joke made me laugh before I could finish it. Which is good 'cause there's no ending." "All right ... that joke is going to be good because I'm going to take all the words out and add new words. That joke will be fixed."

Once, when being handed a drink mid-joke, a joke that was foundering anyway, he just cut the joke off: "That'll fuck up a joke!" A joke about fucking up a fucked-up joke.

After his breakout at the "Just For Laughs" festival, Hedberg got a $500,000 development deal with Fox and appeared on Letterman several more times. (It's widely noted that he was appreciated not just by his peers but also by old-timers like Letterman and George Carlin.) He financed his own movie, a subtle tribute to his restaurant days called Los Enchiladas. Neither the movie nor the development deal bore any real fruit, and yet his appeal grew: underachievement as achievement. In late '98, The Austin Chroniclesaid plainly what many others could only bring themselves to imply: "At the age of 30, he's poised almost to become a spokesman for a generation." The whole story of Mitch Hedberg is in that "almost."

With disarming subtlety, he deconstructed the stand-up form by taking on hackneyed subjects and turning them on their head, or by bombing deliberately: "I play sports. ... No, I don't, what the fuck?" "Remember that show My Three Sons? It'd be funny if it was called My One Dad. ... Wait, what?" "I just bought a two-bedroom house, but I think I get to decide how many bedrooms there are, don't you?" In the context of trippy non-sequiturs about koala infestations and potato chips, this came off as subversive. He was blowing himself up, along with everyone in the room.

The self-destruction extended to his personal life. At first it seemed as if Hedberg's riffing on his drug use was more of a dig at his stage persona, accommodating the various stripes of substance abusers who seemed to cling to him: "I used to do drugs. I still do, but I used to, too." "My manager saw me drinking backstage and he said, 'Mitch, don't use liquor as a crutch.' I can't use liquor as a crutch, because a crutch helps me walk. Liquor severely fucks up the way I walk." "Some people think I'm high on stage; I would never get high before a show, because when I'm high, I don't wanna stand in front of a bunch of people I don't know."

But his unconventional lifestyle, even for a comic—stretches off the grid; living out of hotels or out of the RV he bought with his wife, comic Lynn Shawcroft; avoiding meaningful human contact with anyone besides Shawcroft—led some people to think there was something wrong. In May 2003, after a show in Austin, Texas, Hedberg was arrested for possession of a controlled substance. He spent two-and-a-half days in jail, followed by six months in a hospital, supposedly for treatment of a leg badly mangled by heroin injections. When he was featured in the Los Angeles Times later that year, opening for Lewis Black and Dave Attell, he seemed less repentant than detached. (And he was walking with a discernible limp.) Two years later, of his never-ending tour, he said, "I'm trying to make it hedonistic yet professional." That piece was published three months before he died.

Upon his death, his friends by and large circled the wagons, saying that they didn't see this coming—Mike Birbiglia, who performed with Hedberg, told Dan Fierman in Entertainment Weekly: "People would go, 'Mitch is going to die' and I was like 'Oh, I don't know.' He seemed to pull it off. He had this invincibility to him." But his fans noticed, even as they functioned as a codependent. Toward the end of his life, he would walk on stage with two plastic cups that were widely known to contain alcohol and at least once specifically identified as screwdrivers. Hedberg had killer sets and … less successful sets—some lacked verve, some lacked direction, and sometimes he just couldn't remember his jokes at all. Sometimes, his fans would holler out the jokes he was trying to tell to help him out. It was interactive stand-up, Gallagher for the highbrow, chemically dependent set. (Hedberg told The Onion in 2004 that he was once a Gallagher fan.) In a sense, Hedberg's audience was his greatest enabler.

It should be said that even on the good nights, people sung along to the choruses. They'd often step on his punchlines. Hedberg had so fully seduced his fans that the division between stage and seats fell away. "Didn't you ever hear of dramatic pause?" he'd sometimes grouch.

But that was just the point: His fans weren't attuned to the artifice of performance so much as they were there for communion. That Hedberg is even more popular now then he was in his lifetime is evidence that his material—his act—was more akin to gospel than it was to vaudeville. It's easy to say he was ahead of his time, but more realistically, he was just ahead of YouTube's time. Hedberg was a comedian built for the modern era, an era of online video streaming, of one- and two-liners on Twitter, of Facebook likes and Gmail forwards. He was successful in defiance of the standard sequence in which a comedian gets hot, gets a TV or movie deal, then settles comfortably into the American middlebrow. He couldn't be that comic, in part because of the inscrutability of his material and in part because of the instability of his person, but he could certainly find a place for himself on the margin, busting on comedy's conventions. He could make a career—could make a religion, really—out of almost.

And that, subliminally, is why audiences loved him—not because he wouldn't be those other comics, but because, like the rest of us, he couldn't. Because, like us, he was awkward, he was troubled, he was less than he should have been. His opening joke at "Just For Laughs" said it all: Upon being introduced as a comedian who'd been on Letterman twice, he said: "Two million people watch that show and I don't know where they are. You might have seen this next comedian on the Late Show, but I think more people have seen me at the store. That should be my introduction. 'You might have seen this next comedian at the store.'" He connected with audience on a level all comics aspire to, and that's partly what made him a Comic's Comic, but it was more than that. It was the way he managed to occupy every corner of his comedy, the way he made every piece of it his own, for better and for worse. He was the comedian, and he was the crowd, and he was the room, and he was the wall, and he was the sledgehammer being swung at it, and he was the rubble, too.